Microsoft Chicago build 4.00.244 crashes VirtualBox on startup

I made a VM to install Chicago build 244 (not debug). I did an upgrade from Windows 3.1. When the setup finished, i restarted the VM and launched Chicago. When the startup screen loaded, the VM crashed. What can I do?


  • @user27394967
    VirtualBox isn't good for Chicago builds, 86Box and PCem work perfectly.
  • @jonirob Is VMware good for Chicago builds?
  • @user27394967
    You really need to use an emulator, I've just tested build 224 in 86Box and it installs with no problems as an upgrade from Windows 3.1.

  • @jonirob What confugiration settings do I have to change for the 86box VM to run Chicago?
  • @user27394967
    My 86Box configs:

    Machine: [486 ISA] AMI 486 clone
    CPU: Intel i486SX/16
    Memory: 32 MB
    Time Sinchronisation: Disabled
    Display: [ISA] Trident TVGA8900
    Input Device: Microsoft Serial Mouse
    Sound: [ISA] Sound Blaster 16
    Hard Disk: IDE (0:0) Sectors 63 Heads 16 Cylinders 1224
    Floppy Drive: 3.5" 1.44M
    Other removable devices: Bus: ATAPI Channel: 0:1 Speed 8x.

  • edited July 2021
    @jonirob I'm using 86Box version 3.0, and some of the settings are different. I couldn't set the VM.
    EDIT: Forget it. I'm downloading 86Box version 2.7.
  • edited July 2021
    Use any 486 machine with the default CPU and it should work.
    Failing that you may find PCem easier.
  • edited July 2021
    @jonirob I installed Windows 3.1. BUT THE D DRIVE JUST DOESN'T SHOW UP! What do I do?
  • edited July 2021
    You need to install the cd rom driver in DOS,
  • @jonirob I did all that and installed Chicago build 224, but it still shuts down itself when it starts, just like what happened in VMware. Maybe it's a problem because i upgraded from the IBM OEM release of Windows 3.1?
  • @user27394967
    You can also skip Windows 3.1 and do a clean install using a Windows 95 boot disk.
  • @jonirob How do I do that?
  • edited July 2021
    At the A: prompt type fdisk (enter), go through the defaults, restart, type format c: (enter) type Y (enter). Then go to the CD drive, (either R or D), type setup (enter), that's it.
  • edited July 2021
    @jonirob I DID IT!!!! But the 86box window becomes extremly wide. What can I do to fix it?
    EDIT: I managed to change the size, the wallpaper broke tho (the default was the windows setup background wallpaper)
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